Shelter Island Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩234,741 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Where to stay in Shelter Island
Menantic Creek
If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Shelter Island Historical Society and Sunset Beach.
Find the Best Shelter Island Vacation Packages
Shelter Island Beach Vacation
There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town center on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometers away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.
Shelter Island Hotel Deals
Gurney's Montauk Resort & Seawater Spa
Fabulous location. Woke up to the sound of waves every morning. A short walk from the room to the beach.
Reviewed on Mar 26, 2026
Montauk Manor
clean room
Reviewed on Mar 26, 2026
Water's Edge Resort & Spa
The room was perfect, staff was excellent, parking was right next to my room. Best Breakfast Sausage ever.
Reviewed on Mar 24, 2026
Discover the most popular places to visit in Shelter Island
Havens House
You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.
